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Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs.

ABSTRACT: Methyl and ethyl thioether groups were introduced at all primary positions of ?-, ?-, and ?-cyclodextrin by nucleophilic displacement reactions starting from the corresponding per-(6-deoxy-6-bromo)cyclodextrins. Further modification of all 2-OH positions by etherification with iodo terminated triethylene glycol monomethyl ether (and tetraethylene glycol monomethyl ether, respectively) furnished water-soluble hosts. Especially the ?-cyclodextrin derivatives exhibit very high binding potentials towards the anaesthetic drugs sevoflurane and halothane. Since the resulting inclusion compounds are highly soluble in water at temperatures ?37 °C they are good candidates for new aqueous dosage forms which would avoid inhalation anaesthesia.

SUBMITTER: Becker LF

PROVIDER: S-EPMC4273231 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs.

Becker Lisa F LF Schwarz Dennis H DH Wenz Gerhard G

Beilstein journal of organic chemistry 20141209

Methyl and ethyl thioether groups were introduced at all primary positions of α-, β-, and γ-cyclodextrin by nucleophilic displacement reactions starting from the corresponding per-(6-deoxy-6-bromo)cyclodextrins. Further modification of all 2-OH positions by etherification with iodo terminated triethylene glycol monomethyl ether (and tetraethylene glycol monomethyl ether, respectively) furnished water-soluble hosts. Especially the β-cyclodextrin derivatives exhibit very high binding potentials to ...[more]

PMID: 25550759

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